Why These 3 Midwest Lake Getaways Keep Us Coming Back

Wisconsin Dells, WI – Waterpark Capital Meets Natural Beauty

If you’ve ever heard of the Wisconsin Dells, you probably think of waterparks — it is known as the waterpark capital of the US, and with good reason — there are a LOT of waterparks. However, on our visits, we have discovered the Dells have so much more to offer.

Not only are the Wisconsin Dells breathtakingly beautiful, but they’re also a popular vacation getaway, and there are so many other things for families to do. It’s truly the perfect mix of outdoor adventure and over-the-top fun!

Every time we visit, we do something different, while still taking the time to enjoy the area’s beauty. I love that there are plenty of fun activities for kids (and adults) of all ages. Plus, it’s not a bad drive for us, so it’s an easy long weekend!

There are SO many places to stay when visiting Wisconsin Dells, but we typically stay at Christmas Mountain in one of the cottages or cabins. Some of them are a bit dated, but I love the extra space, full kitchens, and especially all the activities on site. We can easily spend an entire day just enjoying the pool, grounds, and other amenities.

If you prefer a spot closer to the water, this lakefront condo receives great reviews — and also features a pool and hot tub on site, as well as a full kitchen. Everything you need!

Younger kids (and many teens) love a good waterpark, so staying at one of the waterpark resorts like Odyssey Dells could be a good option. Although I haven’t stayed here, I’ve visited both the Odyssey Dells (Mt. Olympus) indoor and outdoor water parks several times with my family, and we’ve always had a blast.

Top Lake Experiences in Wisconsin Dells

Although there are SO many fun things to do in the Wisconsin Dells, since today I’m sharing my favorite Midwest lake vacations, I’ll focus on a few of what I think are the top Wisconsin Dells lake experiences.

A great way to get your bearings is a boat tour — just like I often suggest walking or bus tours when visiting a new city, a boat tour is a fun way to start your trip. In the Dells, an obvious choice is one of the Duck Tours. I’ve done them a few times — with my parents when I was a kid and again with my own kids.

If you prefer to explore on your own, consider kayaking in the lower dells of the Wisconsin River. It’s a great way to experience the area’s spectacular beauty up close! Rent kayaks from Dells Kayak and canoe rentals — they will help you determine the best places to visit, and pick you up at the end!

Finally, be sure to end at least one evening with sunset views from one of the many lakeside restaurants. On our last visit, we searched Yelp and came up with Ravina Bay Bar & Grill. It was delicious, had gorgeous views, and we even walked down to the dock to watch the sunset right on the water!

Family Fun Bonus in Wisconsin Dells

Be sure to head into town and explore all the crazy, kitschy attractions you’ll find in Wisconsin Dells. There are plenty of opportunities for miniature golf, quirky museums, and more. Don’t count them out just because they are cheesy. We had a blast waiting out a thunderstorm on one memorable visit to Wizard’s Quest.

Petoskey, MI – A Picture-Perfect Northern Michigan Gem

Petoskey, MI is one of our all-time favorite places — we love it so much that we make a point to visit several times a year, in all seasons! We’ve been heading up there for over twenty years now and especially love it when we can take along friends or family.

With tons of things to do in all seasons, an adorable downtown (that looks like something out of a Hallmark movie), and sparkling Lake Michigan views, there are few places better for a lake vacation than this area in Northern Michigan! We never get tired of visiting.

Nine times out of ten, we stay at Boyne Mountain in nearby Boyne Falls. If it’s winter, it’s the perfect spot for a ski trip, and in the summer, there are activities galore.

If you want to stay IN Petoskey, there are plenty of other choices. My current favorite is the relatively new Marriott. It’s at the edge of town, which makes it easy to get to all the other small towns in the region (Walloon Lake, Boyne City, etc.).

Top Lake Experiences in Petoskey

You absolutely have to spend at least one afternoon enjoying the beach at Petoskey State Park. As someone who loves a good Florida beach vacation, I was floored when I first visited this beach. Except for the water being unsalted (I get the t-shirts now!), it looked and felt a lot like an ocean beach — even with waves!

If you don’t want to get IN the water, consider biking or walking the Little Traverse Wheelway along the lake. It’s a multi-use paved trail that runs from Petoskey to Harbor Springs and also to Charlevoix (both of which are darling towns for shopping, restaurants, etc.). It’s a bit of a ride, so if you aren’t in biking shape, consider renting an electric bike! I think this would be especially fun in the fall when the leaves are beginning to turn.

Whatever lake you explore, when in Petoskey, a must-do is to search for Petoskey stones. These unique stones are found in several lakes in the area and are quite fun to look for. Make sure you have a bucket with some water or submerge them in lake water — that’s the only way to tell if you’ve found one or not!

Family Fun Bonus in Petoskey

Petoskey, Michigan, is a fabulous town for browsing local shops, enjoying tasty ice cream at Kilwins or other local spots, checking out farm markets, and more. There is even a winery trail for the adults (with a few breweries included).

Chicago, IL – City Vibes with a Side of Lakefront Fun

Although most people think of Chicago as a city getaway, it can also be a fun lake experience — after all, it’s situated right along the shore of Lake Michigan! So, if you are thinking a mix of lake and city vibes, Chicago can be a fun option.

When we visit Chicago (and at just three hours from Indy, we visit often), you get the excitement of a big city AND a gorgeous lakefront escape. Although we typically indulge in the city side of things on our visits, it’s fun to mix it up a bit with a lake activity too!

My favorite spot to stay when visiting Chicago is somewhere downtown. I like to be able to park my car and take public transport, or, even better, walk! We often stay at the Hotel Blake, as it’s conveniently located near the lake, a train station, and within walking distance of many attractions.

If you aren’t a city person, consider staying in one of the suburbs. You’ll have to commute into the city via train or car, but you will probably save a bit on hotel rates. Plus, you can extend your getaway and explore whatever suburb you land in. One of our recent favorites is Oak Brook, but we’ve also stayed in Aurora, Naperville and Schaumburg.

Top Lake Experiences in Chicago

If the weather is nice, a long bike ride or stroll along Lake Shore Drive is a must. You’ll get a lovely view of the skyline, and there is always something happening along the way. It’s easy to hop off for lunch or dinner, and there are various park areas for breaks.

Want to get in the water? Or just relax on the beach? Oak Street Beach is your closest option, as it’s located near Navy Pier and surprisingly close to the city’s hustle and bustle. It can get really busy (because it’s so accessible to city goers), so arrive early to secure a spot or expect to deal with crowds. North Avenue Beach is another spot to consider. You’ll still get the skyline views, but it’s a little north of the city. It’s also close to Lincoln Park, which is a great area to explore.

For a different perspective on Chicago, consider taking a waterfront cruise. I particularly like the architecture river ones, but you can also find one on Lake Michigan that focuses on the skyline views. These can be a fun alternative if it’s a little too early or late in the season to visit the beach.

Family Fun Bonus in Chicago

Overall, Chicago is a fabulous choice for a weekend getaway. There are amazing museums, plenty of parks and neighborhoods to explore, and even Broadway shows. My kids experienced their first comedy show in Chicago, and for several years, we had fun attending the American Girl Tea at Water Tower Place. I love this city because there is truly something for everyone to enjoy.

Wrap-Up: Why We Keep Coming Back

Each of these Midwest lake vacation spots holds a special place in our hearts — not just because of the beautiful scenery or the long list of things to do, but because of the memories we’ve made in each one. We’ve watched our kids grow up skipping stones in Petoskey, laughed through rainy afternoons in the Dells, and wandered along Chicago’s lakefront as the city buzzed behind us. These aren’t just places on a map — they’re woven into our family story.

What keeps us coming back? It’s the feeling we get as soon as we arrive — that deep breath, the shift into “vacation mode,” and the excitement of knowing we’ll experience something familiar and something new, all in one trip. Whether we’re packing up for a weekend escape or adding a few extra days to a summer road trip, we always know we’re in for something special.

And perhaps the best part? All three of these destinations are easy road trips from our home base in Indiana. That accessibility makes spontaneous getaways and intentional family time all the more doable — and meaningful.

So if you’re looking for the perfect blend of lakeside beauty, family fun, and unforgettable experiences, I highly recommend giving one (or all!) of these Midwest lake vacations a try. Who knows — maybe they’ll become the places your family keeps coming back to, too.